(2S,3S)-2-(tert-butoxycarbonylamino)-3-(5-cyano-2-nitrophenylamino)butanoic acid → (2S,3S)-3-(2-amino-5-cyanophenylamino)-2-(tert-butoxycarbonylamino)butanoic acid

HRID 1486083Notes

Reaction equation

HRID 1486083 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:13]([NH:15][C:16]1[CH:21]=[C:20]([C:22]#[N:23])[CH:19]=[CH:18][C:17]=1[N+:24]([O-])=O)[CH3:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.CCOC(C)=O>[NH2:24][C:17]1[CH:18]=[CH:19][C:20]([C:22]#[N:23])=[CH:21][C:16]=1[NH:15][C@@H:13]([CH3:14])[C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 72712348(2S,3S)-2-(tert-butoxycarbonylamino)-3-(5-cyano-2-nitrophenylamino)butanoic acid

Product 1

HCID 72712568(2S,3S)-3-(2-amino-5-cyanophenylamino)-2-(tert-butoxycarbonylamino)butanoic acidYield 99.7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (2S,3S)-2-(tert-butoxycarbonyl amino)-3-(5-cyano-2-nitrophenylamino)butanoic acid (5.35 g, 14.7 mmol) and PdC (10% dry basis, wet, 50% water) (535 mg, 251 μmol) in MeOH (60 ml) and EtOAc (60 ml) was shaken under H2 (50 PSI) for 4 h, then filtered through a bed of celite and concentrated to afford (2S,3S)-3-(2-amino-5-cyanophenylamino)-2-(tert-butoxycarbonylamino)butanoic acid (4.9 g, quant.) as a dark brown solid.

Workup

  1. filtrationfiltered through a bed of celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a01bf6bcdc584420a488619a0dde7d79
Source dataset
uspto-grants-2016_08
Patent number
US09422331B2

Reaction notes

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